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Question

For an unambiguous single step synthesis of the following target molecule (TM), the best bond disconnection in its retrosynthetic analysis is
 

The correct answer is

To determine the best bond disconnection for the retrosynthetic analysis of the target molecule (TM) provided, we need to envision how the molecule can be broken down into simpler starting materials through logical disconnections that will allow easy synthesis. The given molecule is an ester derivative with two ethoxycarbonyl groups attached to a cyclohexanone ring.

Let's analyze the possible bond disconnections:

  1. The first option involves breaking the bond between the two ethoxycarbonyl groups and the cyclohexanone ring. However, this bond disconnection does not provide the most straightforward route to synthesize the target molecule.
  2. The second option involves breaking the bond between one ethoxycarbonyl group and the cyclohexanone ring. This bond disconnection aligns with the formation of an ester linkage and facilitates using readily available reagents such as diethyl carbonate and cyclohexanone.
  3. The third option might introduce complexity in synthesis due to steric hindrance or multiple reaction sites.
  4. The fourth option is similar to the first and does not lead to an effective synthetic pathway.

The correct bond disconnection for a direct and unambiguous single-step synthesis is illustrated below:

This choice best represents a feasible synthetic approach, utilizing straightforward esterification reactions. Diethyl carbonate, when reacted with cyclohexanone, can form the ester linkage by a nucleophilic acyl substitution mechanism, which is efficient and commonly used in organic synthesis.

Hence, the correct answer is:

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Important Questions from Organic Synthesis

  1. The major products X and Y formed in the following reaction sequences are

  2. For the following reaction, the possible product(s) is/are

  3. The reaction(s) that yield(s) X as the major product is (are) 

  4. The major products E and F in the following reaction sequence are 

  5. Consider the following reaction sequence. The correct option(s) is (are)

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